$728,879Average Value$372Average Price per Sq Ft36Homes For Sale
Serene residential area in Guilford with various homes nestled among lush greenery.
A place with something for everyone
Guilford is a coastal Connecticut town that, at first glance, resembles a small town reminiscent of a 1960s-era television show. With its quaint and historic downtown sector lined with quaint local retailers, the 12-acre Guilford Town Green that is the site of various performances throughout the year and the quiet, tree-lined streets, Guilford provides an almost country feeling, like something out of a brochure for a New England bed-and-breakfast. But look a little closer and it’s also a vibrant, cosmopolitan town with a bevy of amenities, superb schools and beautiful homes, not to mention the fact that Guilford abuts Long Island Sound on its southern border, affording residents easy access to the beach and the ocean beyond. “People come here because they want waterfront and seclusion,” says local Realtor Karen Stephens of Compass, who has been representing transactions in the area for more than 20 years. “And the properties are quite amazing.” It’s that combination of qualities that leads Guilford First Selectman Matthew Hoey to describe Guilford as “a place with something for everyone.”
Out and about in Guilford
Because of its proximity to Long Island Sound, Guilford is a haven for lovers of the sea. Mariners can keep their vessels at the Guilford Marina, and members of the Guilford Yacht Club can access both slips and moorings, as well as the club’s tennis, dining and other social facilities. Jacob’s Beach is a 25-acre coastline retreat on the Sound, where kids can play on the playground and visitors of all ages can enjoy the open, sandy beach and grassy space perfect for sunbathing or a picnic. Further inland is Lake Quonnipaug, a prime spot for catching a variety of freshwater species, and also a perfect spot for swimming or relaxing on the lakeside beach. Hikers head to Timberland Preserve, a 600-acre expanse with more than 15 miles of trails, and golfers can tee off at the nine-hole Guilford Lakes Golf Course.
The centrally located Guilford Town Green is a favorite community gathering spot, serving as the site of a summer concert series, the town’s annual Halloween and holiday tree-lighting festivals, the GreenStage Guilford Live music festival and a variety of other programs throughout the year. “People come from all around for these events,” says Stephens. And don’t be too surprised if exotic animals suddenly appear on the Green, as a local anonymous artist periodically places two-dimensional (although quite lifelike) replicas of polar bears, penguins and other Arctic-dwelling animals on the Green to celebrate the season’s first snowfall. After residents have had a chance to see the art installation, the animals are auctioned off to benefit Meals and Wheels.
Serene beachside park located at Jacob's Beach in Guilford overlooking a tranquil sandy beach.
Bittner Park in Guilford features calm areas to host picnics with the family.
Serene landscape of Guilford showcasing a tranquil marsh with golden tall grass.
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Top-rated schools
The Guilford Public Schools district earns an overall grade of A from Niche, and the area’s exceptional schools include A. W. Cox Elementary, Adams Middle and Guilford High School, all of which earn an A from Niche. Students at Guilford High School have the opportunity to participate with more than 35 school-sponsored clubs, can audition for the school’s award-winning theater program and have the opportunity to play more than 15 varsity-level sports. There are also several renowned private schools in the area, including nearby Choate Rosemary Hall, ranked as the best private school in the state by Niche, which gives it an A-plus rating.
Guilford Lakes School is conveniently located on Maupas Road.
Students are proud to call Guilford High School their place for learning.
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From 18th century colonials to modern homes
Guilford has the distinction of being home to one of the largest collections of historic homes in New England, including the 1693 Henry Whitfield House, that today serves as a museum. The Whitfield House is the oldest house in Connecticut and the oldest stone dwelling built by North American settlers. And while buyers will find homes here for sale that were built as far back as the 18th century, there are plenty of options for those who prefer new construction, too. The median price in the area is $590,000, and buyers should expect to pay an average of $341 per square foot. A two-bedroom/two-bathroom ranch-style home in need of some TLC can sell for as low as $200,000, and prices can go up to nearly $6 million for a four-bedroom/three-bathroom colonial on a private waterfront peninsula with a private beach.
Picturesque Colonial style home in Guilford with a vibrant blue door and a cozy porch.
Two story home in Guilford with a neat driveway and a calm street in the foreground.
Modern home in Guilford with a manicured lawn and a calm ambiance in the background.
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Plentiful options for shopping and dining
With Big Y located in the center of town, residents don’t have to drive far for grocery shopping trips, and Bishop’s Orchards offers the opportunity for visitors to pick their own fruit in-season, typically from June through October. Walmart is located next to Big Y for any home necessities. Downtown Guilford has an array of local boutiques and shopping opportunities, and the Connecticut Post Mall – the largest mall in the state – is located in Milford, just over 20 miles away.
When dining out, Guilford Mooring is a popular destination for fresh seafood served in a waterfront setting. For a little more upscale occasion, Chapter One is well-known for exceptional service and a wide-ranging menu featuring burgers, steaks and seafood, as well as vegetarian and vegan options. And for a little grab-and-go, Cinco de Mayo Food Truck located at the north end of Guilford Town Green prepares well-known Mexican favorites for a relaxing lunch in the park.
Residents of Guilford enjoy strolling on vibrant streets featuring quaint local businesses.
Lobster Pound in Guilford is known for their incredible Hot Lobster Roll.
Charming town of Guilford as pedestrians stroll past boutique storefronts.
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Getting out of town
Commuters here have easy access to Interstate 95, which bisects the middle of Guilford, make the 16-mile trip to New Haven. Alternatively, the CTrail Shore Line East train leaves from the Guilford Station, with service to New Haven taking about 20 minutes, where riders can connect to trains going south to New York City or north to Boston.
Guilford Train Station offers residents direct access to neighboring towns and cities.
Guilford Train Station provides easy commuting for residents into New Haven.
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Photography Contributed By
Fabio Riso
Video By
Matthew Bloch
Interested in learning more about homes in this area?
Reach out to
Cathy Lynch,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Guilford, CT sell after 67 days on the market compared to the national average of 55 days. The median sale price for homes in Guilford, CT over the last 12 months is $635,000, up 7% from the median home sale price over the previous 12 months.
Welcome to 296 Valley Shores Drive. Easy living in this 3-bedroom, 2 bath ranch style home in a water area community awaits! This property invites you in through the double front doors, impressive floor to ceiling brick fireplace, vaulted ceilings, and expansive back deck with access from living room, kitchen and primary bedroom. The charm doesn't stop with a lightly treed lot and babbling brook
Turn-key with peaceful marsh views, just 0.5 mi from the vibrant Guilford Town Green! Enter through the picture-perfect front screened porch- an idyllic spot to sip morning coffee or unwind in the evening while overlooking cascades of hydrangeas and serene West River marsh scenery. Inside, this meticulously maintained and thoughtfully updated Cape Cod blends timeless charm with modern comfort.
Exceptional Investment Opportunity - Prime Guilford Location Just steps from the vibrant Guilford Green, this historic multifamily property features two spacious 2-bedroom, 1-bathroom units on a level 0.46-acre lot. (Field card Says 2 bedrooms in each apt -4 bedrooms total- In 1st floor apt. Front room was used as 2nd bedroom. Fireplace is not currently operational. Ideal for restoration, it
Nestled on a quiet cul-de-sac in the sought-after Copper Hill Village, this detached Cape-style condo offers the privacy of a single-family home with the effortless lifestyle of a managed community. Boasting 1,459 square feet of bright, airy living space, this 2-bedroom, 2-bathroom residence is designed for comfort and versatility.The heart of the home features a living area with a cozy
Welcome to 154 Wilbur Ln, a truly distinctive property that sets itself apart from the rest providing over four and half acres of privacy. This home boasts five spacious bedrooms and two full baths, along with a large versatile studio or den that provides additional options for your needs. As you enter, a convenient mudroom is to the left and down the hall leads you into the kitchen where you
Discover the vibrant energy of the historic town green just outside your doorstep. The inviting sidewalk guides you to the lively center, only 600 yards away. There, you'll find a treasure trove of quaint shops, restaurants, the recreational center, and cozy coffee spots to enjoy. Join in the community spirit at concerts and local events, and explore the area's rich history and character-all
Built by a highly regarded shoreline builder known for uncompromising attention to detail, this residence is designed for buyers who appreciate elevated finishes, enduring quality, and effortless livability. The home features an open floor plan with white oak hardwood floors, 9-foot ceilings, custom millwork, and oversized Pella windows throughout. A stunning bluestone entry leads to an elegant
Mixed-use zoning (convertible to full commercial with town permits) 2,005 sq ft total / 1,672 sq ft finished living space..30 acre lot with generous parking (10+ vehicles) Year built: 1893 with numerous modern updates. Rare to find a house in Guilford with "public water". Current layout: First Floor: Professional medical office space, 4 office space + half bath Second Floor: 1-bedroom apartment,
Here is your opportunity to build this beautifully designed 2,814 sq ft Cape-style home privately situated on a rear lot! This thoughtfully crafted To Be Built home blends classic New England charm with today's clean farmhouse aesthetic - board-and-batten accents, striking black windows, and timeless architectural lines. The open-concept main level is designed for today's lifestyle, featuring a
New Development. 25 units. Now under construction, Units over 2200 sqft. Full Basement and 2 car garages. Walking distance to town. 3 models to pick from with various locations throughout subdivision.
Enjoy living in one of CT's most coveted historical treasures, the Pelatiah Leete House! Perched on a private, sweeping knoll with WATERVIEWS of Shell Beach Lagoon running into Long Island Sound, (located across the road) this Colonial Home is as close as one gets to genuine American History. Only 5 families have inhabited this 1710 English Post & Beam home that has survived Colonial Times & a
Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich
Rarely do you find such a gem as the upcoming construction on Blue Hills Dr! Nestled in a tranquil neighborhood at the end of a cul-de-sac and surrounded by lush woods, this under construction home promises to be your dream home. No expense was spared in this perfectly done dream home. Handsome hardwood floors and recessed lighting run through this entire home, enhancing all of the other features
Welcome to 296 Valley Shores Drive. Easy living in this 3-bedroom, 2 bath ranch style home in a water area community awaits! This property invites you in through the double front doors, impressive floor to ceiling brick fireplace, vaulted ceilings, and expansive back deck with access from living room, kitchen and primary bedroom. The charm doesn't stop with a lightly treed lot and babbling brook
Ideally located in the heart of downtown Guilford, 26 Water Street is now officially available. Situated within the Guilford Green District, this property offers exceptional versatility with a wide range of permitted uses (see attached zoning regulations, Section 4.1). The existing use may continue as a non-conforming use if desired. The current layout is configured similarly to a multi-family
Property Id: 2312581Experience impeccable craftsmanship in our elegant village of luxury apartments. The moment you enter this whimsical retreat, you'll feel an immediate sense of calm, connection, and security. Blending country soul with a contemporary edge.Beautiful views abound in our outstanding modern, one bedroom apartment that features a beautiful spacious bedroom, ample
Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich
Property Id: 2312572Experience impeccable craftsmanship in our elegant village of luxury apartments bordering a land preserve. The moment you enter this whimsical retreat, you'll feel an immediate sense of calm, connection, and security. Blending country soul with a contemporary edge.Beautiful views abound in our one bedroom apartment that features a beautiful spacious bedroom,
Charming 3 bedroom, 2 full bath home totally renovated. Master bedroom with full bath on main level, two additional bedrooms and full bath on second floor. Natural gas heat, central air conditioning. Owner provides lawn care and snow removal. Washer and dryer in kitchen, new energy efficient furnace, solar electric, city water, located on just over an acre with a three bay storage building at the
Property is available March, 2026 through November 21, 2026. Spend the 2026 season less than .5 miles away from the Guilford green. This serene home is located on an interior lot, offering privacy, yet proximity to all the Guilford has to offer. The home provides one level living, with one bedroom, plus a study. The great room, with wood-burning fireplace is spacious and functions as both living
One-year furnished rent available starting June 1st, in desirable Guilford CT. Split Level home located on the west side of town with very convenient access to New Haven, shopping and restaurants. Completely furnished with 1 car attached garage. Main living level has an inviting front room with an open concept kitchen, dining room and family room. There is quick access to the patio. There are two
Recently converted from one family to two family. New kitchen, appliances, paint, and flooring. Includes a stack washer/ dryer. Walk to Town! Includes heat and water! Two bedroom. Second floor.
Live in the heart of downtown Guilford! This spacious 3-bedroom, 1-bath apartment sits directly across from the iconic Guilford Green, offering unbeatable walkability to shops, restaurants, cafes, and town amenities. The unit features updated finishes, central air, and the convenience of in-unit washer and dryer. Enjoy private off-street parking and low-maintenance living with cold water, sewer,
A FULLY FURNISHED, SHORT TERM RENTAL, 103C Boston Street is a FULLY FURNISHED light-filled townhouse, in the historic Guilford Elementary School building, with large windows & 12 ft ceilings. Bespoke furnishings, and high quality kitchen equipment, all within walking distance of the Guilford Green. AVAILABLE for a term of 4-6 Months. Very close to the shops, library, restaurants and everything
ANNUAL RENTAL - FURNISHED OR UNFURNISHED WATERFRONT HOME. Come and enjoy year round this classic New England waterfront home located in coveted Sachems Head with room for everyone- especially your four legged family members. This wonderful home offers a lifestyle for your whole family to enjoy. There are water views from most every room as well as beautiful outdoor spaces to sit and enjoy the
Available 1/15 - 6/15. Discover a rental like no other where privacy and convenience delightfully collide! This extraordinary 17-acre estate adjoins the expansive 600-acre East River Preserve and Guilford Land Trust lands, offering a secluded haven of total privacy mere minutes from the historic Guilford Green, the sandy stretches of Jacobs Beach, and the accessibility of I-95. The estate's heart
AVAILABLE MARCH 1, 2026 FURNISHED ANNUAL RENTAL...DIRECT WATERFRONT WITH NEW DOCK !! Leete's Island & Joshua Cove...a PADDLER'S PARADISE in a welcoming beach community... Catch amazing sunrises from this great location! Swim right from your beach or dock! This updated 2 Bedroom, 1 Bathroom Cottage is absolutely adorable, with incredible views of Joshua Cove through large bay windows. Totally
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